


Friends With Benefits

by lydslibrary



Category: Supernatural
Genre: Anal Sex, Dom!Sam, Dom/sub, Double Penetration, Eiffel Tower, F/M, Fingering, No Wincest, Oral Sex, Punishment, Rough Oral Sex, Rough Sex, Smut, Spanking, Threesome, dom dean and sam winchester, dom!Dean, pure rough hardcore smut is what this is, this is so smutty it's not even funny
Language: English
Status: Completed
Published: 2020-11-10
Updated: 2020-11-10
Packaged: 2021-03-09 03:02:52
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,529
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27497644
Author URL: https://archiveofourown.org/users/lydslibrary/pseuds/lydslibrary
Summary: You're being a brat after Sam and Dean saved your ass on a hunt and they're more than a little fed up with your attitude.
Relationships: Dean Winchester/Reader, Dean Winchester/Reader/Sam Winchester, Sam Winchester/Reader
Comments: 1
Kudos: 161





	Friends With Benefits

**Author's Note:**

> That scene in 8.15 (Man's Best Friend With Benefits) where Dean and Sam both agree that the familiar is hot... yeah... somehow that inspired this, and I'm not mad about it.

You were filled with rage as you followed the brothers into the motel room that the three of you were sharing.

“WHAT THE HELL?” You yelled, as you closed the door behind you. “The two of you _have_ to stop treating me like a child!” The hunt that you all had just gotten back from was a successful one, no thanks to you. Sam and Dean were having a hard time letting you lead the way when it came to hunting, and this was technically your hunt. You found the case, you read the lore, you even paid for the motel room.

“Hey, we saved your ass,” Dean said nonchalantly, ignoring your tantrum completely. Sam was doing the same as he began packing up his duffle bag.

“I was fine! I would have seen him!” You said, in reference to the vamp that would have probably turned you had Dean not beheaded him first. You knew they saved your ass; you were just mad that they were even there to save it. Per your plan, they were supposed to raid the inside of the nest while you took care of the outside. Dean saving your ass meant that, as usual, the two of them totally ignored your plans. They had absolutely no respect for you as a hunter, and it was making your blood boil. You took a deep breath and began making your way towards Dean, who was now standing next to Sam, both of them smiling cockily as you stormed over to them. You jabbed your finger into Dean’s chest, your face inches away from his. “You listen here, Dean. _I know_ you saved my life, okay? I am grateful for it. But I am so sick and tired of you – and you,” you said, pointing to Sam, before jabbing your finger back into Dean’s chest, “ignoring my plans. The two of you never listen to me and I swear to God, if either of you do it again, it will not end well for you,” you finished sternly. You looked at Dean for a response, only to see an expression on his face that was hard to describe. “What?” You spat.

“That was incredibly hot,” Dean mumbled. You rolled your eyes and looked at Sam, who tended to be the more serious one in these situations.

“It was pretty hot,” he shrugged.

“You two are fucking _impossible_ ,” you huffed, crossing your arms over your chest in disbelief. They _still_ weren’t taking you seriously.

“Hey, watch your attitude,” Dean warned, giving you a look.

“And if I don’t? What are you gonna do about it?” You retorted. You would usually never talk back to Dean like this; you’d be over his knee in a heartbeat had the two of you been alone. The two of you weren’t exclusive; you just helped one another scratch those itches on occasion. Okay, maybe it was more like three to four times a week. Better than risking an STD with some random stranger at a bar, right? Plus, Dean knew what you liked. He knew how to please you, and you trusted him to dominate you – which was something he loved to do. However, he’d never done it in front of Sam, which is why you weren’t concerned with Dean’s warning. It’s not like he was going to pull you over his knee in front of his brother. Not that Sam didn’t know about the arrangement that the two of you had.

“Y/N,” Dean warned again.

“No, both of you can fuck all the way off,” you spat.

“HEY!” Sam bellowed, catching you off guard. You took a few steps back as you watched the giant come towards you, a look in his normally kind eyes that you had never seen before. It wasn’t anger it was… it was the same look that Dean got when you had pushed him a little too far. “Listen to me,” Sam hissed, as he stopped inches in front of you, bending down a little to get on your eye-level. You gulped. You had always thought Sam was attractive – that was undeniable. You weren’t sure what was in the Winchester genes, but God damn – it wasn’t fair. You had never thought about sex with Sam, though. You were always so preoccupied with the older Winchester; you didn’t really have time or reason to think of the younger one in that way. However, with the air of dominance he was giving off… only inches away from your face… yeah, you were definitely thinking about sex with Sam. “You better lose the fucking attitude, Y/N, or I swear to God _I’ll_ pull you over my knee if he doesn’t,” Sam growled, pointing to his brother who was watching with a smirk on his face. Your clit pulsed at the thought of both of them dominating you.

“Oh, will you, now?” You asked, both sass and intrigue in your tone. You fully intended on pushing him as far as you could.

“I’d tread carefully, Y/N. He’s a lot less forgiving than me,” Dean said, amusement lining his voice. He knew you’d ignore him. He knew you’d continue pushing. You turned to look at Dean.

“Shut up,” you snapped, Dean’s eyebrows raising in response. You were in for it now.

“Yeah, you’re done. Come here. _Now_ ,” Dean ordered, pointing to the ground in front of him. You rolled your eyes – another thing that you were sure you’d regret doing later, but right now you were having too much fun – and pushed your way past the taller Winchester to come to stand in front of the shorter one. Dean looked at Sam over your shoulder and nodded slightly, as if he was giving him permission to do something, which you were sure you’d find out about shortly. Dean turned his attention back to you, lust and dominance in his eyes. You could feel the heat in your core begin to rise just with that one look. Dean huffed as he pushed you down to your knees and a smile spread across your face. You had no idea what to expect, but you were excited. “Take my belt off and bring it to Sam,” Dean commanded. You obeyed, beginning to regret being such a brat. You’d been spanked by Dean plenty, and sure, you didn’t mind it. You loved it, actually. But Dean knew your limits. He knew how hard or soft to hit, he knew what spots hurt more than others – Sam didn’t. And if Sam was going to be the one punishing you – with a _belt_ – you only hoped that he didn’t hit as hard as it looked like he could hit. You took Dean’s belt off and stood up, walking over to Sam, who was now sitting on the edge bed. You placed the leather in his outstretched palm and he patted his knee, signaling you to bend over it. You did as you were told, feeling your pussy begin to clench around nothing.

“You know,” Sam began, rubbing your denim-clad ass with his large hand, “Dean and I saved your ass, right? And being a brat isn’t really the best way to go about thanking us, wouldn’t you agree?” Sam asked, getting Dean’s belt ready.

“Yes,” you replied, the smile was audible in your voice. Dean suddenly appeared in front of you, his nose almost touching yours as he grabbed under your chin with his hand, his fingernails digging crescent moons into your cheeks.

“You address him the same way you address me, do you understand?” Dean growled.

“Yes, sir,” you gulped. You wiped the smile off your face but the excitement within you only grew. You were both terrified and looking forward to what was about to happen to you.

“How many do you think she needs, Dean?” Sam asked, now dragging the leather along your backside. At least you were still wearing jeans – not that they’d last very long. Dean let go of your face and stood up straight, leaving your field of vision.

“I’d start with 20 at this point, and if it still seems like she needs more then we can add on from there. How does that sound?” Dean asked you. You nodded in response, your mind reeling with the thought of 20 swats with the damn belt. You shouldn’t have been such a brat. You felt the brothers look at each other and shake their heads before you realized that you had forgot to respond verbally. You looked behind you and watched as Dean pulled your jeans and panties off in one swift motion. Sam noticed you watching and grabbed your head, forcing you to look down at the floor.

“Speak when spoken to. Make it 30, Sammy. Does that sound fair?” Dean asked.

“Yes, sir,” you replied. You could feel your juices leaking out of you as you waited anxiously for the first hit. You winced at the sting that the leather strap left on your bare ass. You knew Sam was only warming up; he wasn’t hitting as hard as you felt like he could. Dean came back around into your field of vision again as Sam delivered another spank to your ass. Dean grabbed your chin and made you look up at him, being that his crotch was what was at your eye-level at this position.

“Take them off,” Dean commanded, motioning to his jeans. You quickly obeyed, Dean’s cock springing up as soon as you had let his jeans fall to his ankles. You smiled devilishly as you wrapped your hand around the base. You loved Dean’s cock. It was your favorite part of him; and he knew how to use it so well. You clenched your legs together as Sam gave you another lick with the belt. “Open,” Dean ordered, softly smacking your face. You smiled and let go of his dick, opening wide for Dean to shove his cock in your mouth, almost hitting the back of your throat. Sam gave you another smack with the belt, much harder than the last however many you had received, and you lurched forward taking all of Dean in your mouth. You suppressed a gag as Dean wrapped a hand in your hair, holding you down on his cock. This gave you time to feel how on fire your ass actually was; you had no idea how many swats Sam had delivered but you weren’t sure how many more you could take. “What are we at Sammy?” Dean asked his brother casually, as if his cock wasn’t buried deep in your throat.

“Twenty,” Sam replied. Ten more. You could take ten more.

“Count the last ten,” Dean commanded. He hadn’t moved, he was just holding you there, down on his cock, letting you taste him, and you were sure that your juices were running down your thighs at this point. Sam spanked you again, and you let out a “one” to the best of your ability. Dean didn’t loosen his grip on your head one bit. After the eighth hit, you had tears welling up in your eyes, partly from the spanking and partly from the fact that it was hard to breath with Dean’s entire cock in your mouth and you had to keep suppressing a gag. Another hit came down and you mumbled a “nine”, followed by another as you felt a tear run down your cheek and managed to get out a “ten”. “Good girl,” Dean praised. He finally began to move in and out of your mouth slowly, and you felt Sam put the belt on the bed and start to rub your sore ass. Sam spread your cheeks, leaning over to look in between your soaked folds.

“She’s so wet, Dean,” Sam smiled, sliding a finger in between your folds. You looked up at Dean as his cock continued to slide in and out of your mouth, pleading him with your eyes to do something about your wetness. Dean just smirked.

“Oh, you liked that, huh?” Dean asked, continuing to slowly thrust in and out of your mouth. You tried to manage a “yes sir”, but Dean wasn’t stopping so it came out muffled. You lunged forward as Sam stuck a finger in you, taking all of Dean again. Fuck, it felt good. Dean and Sam both pumped in and out of you at opposite times, making it so that one of your holes was always filled, but never both. Sam added another finger and you moaned, only for it to be muffled by Deans cock hitting the back of your throat. Suddenly, Sam slid out from under you, forcing you to get on your knees if you wanted to keep Deans cock in your mouth, which you did. “Already, Sammy?” Dean asked his brother, as if everything was normal and you weren’t even in the room.

“Hey, you get to fuck her all the time. It’s been months for me, man. I mean, look at her,” Sam said, taking off his jeans and boxers. Dean looked down at you as you continued to suck him off, pulling you off of his cock by your hair and coming down to his knees on the floor in front of you. Dean pushed you down on all fours and placed his cock right back in your mouth. Your cunt was now fully exposed to Sam, who you could feel get on his knees behind you.

“I’m finishing with her pussy if you’re getting a turn at it first,” Dean remarked.

“Fine,” Sam replied as he rubbed your clit with his fingers, causing you to moan.

“Ah, fuck, keep making her moan,” Dean said, throwing his head back. The sound of them having a conversation without even acknowledging you between them made your pussy clench. It was by far the hottest thing you’ve ever experienced – being their little fuck toy. Dean moved his hands to your back, pulling your shirt up so he could unhook your bra and make it easier for him to reach your nipples, which he then attended to by pinching and rubbing them lightly. You moaned again, muffled from Dean’s cock still in your mouth, and as you did so, Sam teased your entrance, which made you gasp around Dean’s dick. “Fuck, that’s so hot,” Dean said, acknowledging you for the first time in a while, earning a shiver from you. Sam finally entered you, forcing you to gag on Dean’s cock in the process.

“Fuck, you’re so tight, Y/N. Is my brother fucking you hard enough?” Sam teased, earning a glare from Dean as he continued to pound into you. You muffled a “yes sir” with Dean’s cock still in your mouth.

“You love when your mouth is full of cock, don’t you?” Dean asked, finally giving you a break from sucking as he pulled his member from your mouth and grabbed a fistful of your hair, tapping his cock on your cheek, rubbing your spit around. Sam continued to thrust into you mercilessly, making it hard for you to reply, but you did.

“Yes, sir,” you replied with a devious smile – you weren’t lying. You did love it.

“Alright, my turn,” Dean said to his brother, as he pulled your hair back forcing you to look up at him, “He’s loosened you up for me, so you better show him how thankful you are while he’s over here, got it? And then maybe we’ll let you come tonight,” he said sternly, his face close to yours.

“Yes, sir,” you smiled, ready to show Sam what your mouth could do. The boys switch positions and Dean wasted no time ramming into you, earning a yelp from your lips. Sam smirked and grabbed your chin, bringing your face closer to his cock, which was roughly the same size as Dean’s, but a little bit longer. You opened your mouth for him, wanting nothing more than to taste his dick covered in your juices. You let Sam fuck your mouth, hitting the back of your throat every time, saliva spilling out of the corners of your lips. You had never experienced anything like what you were experiencing now. Dean and Sam filling you at the same time was so fucking sexy, you could have came from the thought of it alone. Sam pulled his cock out of your mouth with a pop, lightly slapping your face with it.

“Hey, Dean,” Sam began, although his eyes were on you, “You think she’d be able to handle both of us?” Your eyes grew wide at the thought of both of your holes being filled and you felt your pussy contract around Dean’s cock with excitement.

“What do you think, sweetheart?” Dean asked, “You wanna take both of us in these pretty little holes?” You nodded enthusiastically, smiling up at Sam who was smirking down at you. “Get the lube,” Dean said to his brother, and Sam nodded as he got up from his knees to go look through Dean’s backpack for the liquid. Dean pulled out of you and you whimpered at the emptiness. “Strip the rest of your clothes and get on the bed,” Dean commanded, with a firm smack to one of your sore cheeks. You winced at the pain but you listened, discarding your remaining clothes – your t-shirt and unhooked bra – and laying on the bed on your side. Sam came back with lube in hand and the brothers laid on either side of you, Dean facing you and Sam behind you. Dean watched himself guide his cock back into your pussy as he slightly lifted one of your legs for better access, forcing a moan from you. He silenced you with his lips, his tongue entering your mouth. You felt Sam behind you rubbing lube around your hole, and you couldn’t wait for both of them to be inside you again. Sam finally lined his cock up with your back entrance, teasing you with the tip of it.

“Beg for it,” Sam whispered into your ear. You could have came right then. You felt the coil in your abdomen tighten, and Sam wasn’t even inside you yet.

“Please, please fuck me! Please, _sir_!” You begged, hoping that it would suffice. Sam slowly pushed himself into you, eventually finding the alternating rhythm that Dean was in. You felt as though you were floating on air; you were certain that nothing had ever felt this good in your life. You moaned loudly only to be silenced by Dean sticking two of his fingers in your mouth and demanding you to suck. You obeyed, scared to make either of them upset with you; you didn’t want them to ever stop. Sam reached around from behind you and began pinching and rubbing your erect nipples. You were going to cum soon and Dean must have felt your pussy clench and figured out that you were on the edge.

“Don’t you dare fuckin’ cum before we do. And don’t you dare do it without asking,” Dean said sternly, looking you right in the eyes. You nodded and continued to suck on Dean’s fingers, wishing there was a third brother who could fill your mouth with another cock. You felt Sam and Dean’s thrusts becoming sloppier and sloppier, their grunting becoming breathier, and you knew they were both about to come undone. At the same time. Inside you. It took everything you had not to cum at the thought, and as your pussy tightened around Dean’s cock, it was enough to send him over the edge, Sam following shortly after. You felt their warm ropes of cum fill up both of your holes, and with a little help from Dean’s fingers on your clit and Sam’s continued nipple play, the coil inside you was about half a second away from snapping.

“May I please come, sir?” You mumbled through Dean’s fingers that were still in your mouth, glancing at both of them.

“What? Sorry, couldn’t understand you,” Dean smirked, taking his fingers out of your mouth.

“May I please come, sir!?” You repeated, much more desperate this time as you were already holding your orgasm off and the brothers had not stopped moving their fingers. Dean chuckled under his breath at your neediness.

“Go ahead, cum for us,” Dean ordered, but you were already coming before he could finish his sentence. “Go ahead” was all you had to hear. Your orgasm ripped through you as you shouted expletives and came around Dean’s cock, your muscles clenching around both of the cocks inside of you. Sam and Dean continued playing with you until you rode out your orgasm, heavy breaths coming from all three of you as they pulled out of you and laid beside you once you had finished. As you came down from your high, you winced at the pain that was starting to make itself known on your ass and you realized that it’d probably be a week or so before you’d be able to sit or walk properly again. Regardless, it wasn’t going to stop you from being a brat. No, if anything… you were about to test your limits.


End file.
